Chesapeake Holiday Rentals

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Our top choices for Chesapeake holiday rentals

Large Cabin with Stunning View - Fire Pit, Relax & Unwind

Large Cabin with Stunning View - Fire Pit, Relax & Unwind
Gallipolis
9.8 out of 10, Exceptional, (46 reviews)
"The property was in excellent condition facilities and beds were absolutely perfect the view over the river was spectacular the breakfast was delicious "
United States
Samuel H.
The price is NZ$250
includes taxes & fees
21 Apr - 22 Apr
Large Cabin with Stunning View - Fire Pit, Relax & Unwind

The Bunkhouse

The Bunkhouse
Crown City
10.0 out of 10, Exceptional, (28 reviews)
"We really enjoyed staying there. The fishing was good. It was a very clean place to stay"
United States
Jennifer R.
The price is NZ$416
includes taxes & fees
17 Apr - 18 Apr
The Bunkhouse

2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.

2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
Kenova
10.0 out of 10, Exceptional, (44 reviews)
"The place was amazing! "
United States
Sam
The price is NZ$318
includes taxes & fees
17 Apr - 18 Apr
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.

Secluded Ohio Forest Escape at Fuller's Fifty

Secluded Ohio Forest Escape at Fuller's Fifty
Patriot
10.0 out of 10, Exceptional, (84 reviews)
"It was a perfect spot for a quick getaway! "
United States
Patricia
The price is NZ$297
includes taxes & fees
19 Apr - 20 Apr
Secluded Ohio Forest Escape at Fuller's Fifty

Cozy 2-bedroom apartment located next to St. Mary's Hospital!

Cozy 2-bedroom apartment located next to St. Mary's Hospital!
Huntington
10.0 out of 10, Exceptional, (15 reviews)
"Great place, clean cozy love the 2 bathrooms!!"
United States
Katherine D.
The price is NZ$361
includes taxes & fees
19 Apr - 20 Apr
Cozy 2-bedroom apartment located next to St. Mary's Hospital!

Charming 2-bedroom house located in beautiful wooded setting!

Charming 2-bedroom house located in beautiful wooded setting!
Raceland
9.8 out of 10, Exceptional, (10 reviews)
"We really enjoyed our stay, perfect location for a visit to that part of Kentucky."
United States
Melinda K.
The price is NZ$335
includes taxes & fees
19 Apr - 20 Apr
Charming 2-bedroom house located in beautiful wooded setting!

THE LUXURY CABIN IN THE WOODS

THE LUXURY CABIN IN THE WOODS
Catlettsburg
10.0 out of 10, Exceptional, (225 reviews)
"Perfect weather enjoyed our stay "
United States
Kris C.
The price is NZ$583
includes taxes & fees
6 May - 7 May
THE LUXURY CABIN IN THE WOODS

The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.

The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.
Catlettsburg
10.0 out of 10, Exceptional, (121 reviews)
"Cozy Cabin is great. Highly recommend!"
United States
Jason M.
The price is NZ$365
includes taxes & fees
27 Apr - 28 Apr
The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.

Historic & Chic apartment by Arena, University, Hospital - Dog Friendly

Historic & Chic apartment by Arena, University, Hospital - Dog Friendly
Huntington
9.6 out of 10, Exceptional, (5 reviews)
"Comfortable convenient to everything. It was a home away from home."
United States
Kimberly M.
The price is NZ$522
includes taxes & fees
20 Apr - 21 Apr
Historic & Chic apartment by Arena, University, Hospital - Dog Friendly

Whispering Pine's Cabin! NO CHECK-OUT LIST

Whispering Pine's Cabin! NO CHECK-OUT LIST
Patriot
The price is NZ$541
includes taxes & fees
23 Apr - 24 Apr
Whispering Pine's Cabin! NO CHECK-OUT LIST

Pointer Palace

Pointer Palace
South Point
10.0 out of 10, Exceptional, (6 reviews)
"An excellent place to stay. Clean, comfortable, in a safe feeling neighborhood. Probably the most thoughtfully appointed VRBO I've ever stayed in. "
United States
Jon W.
The price is NZ$227
includes taxes & fees
14 May - 15 May
Pointer Palace

Modern Loft-Style Retreat Near Blenko Glass – Milton, WV

Modern Loft-Style Retreat Near Blenko Glass – Milton, WV
Milton
10.0 out of 10, Exceptional, (1 review)
"What a great find in little Milton. It was walking distance to LaBanca (great dinner and drink spot). The accommodations are very modern and well appointed. Bed was comfortable. The host was very responsive and it was easy to add an additional night to my stay. Will absolutely stay there again. "
United States
brandon w.
The price is NZ$418
includes taxes & fees
17 Apr - 18 Apr
Modern Loft-Style Retreat Near Blenko Glass – Milton, WV

Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland

Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland
Ashland
10.0 out of 10, Exceptional, (14 reviews)
"Had a great stay! Cool town!"
United States
Noah S.
The price is NZ$282
includes taxes & fees
27 Apr - 28 Apr
Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland

4Bed/3Bath GREYSTONE COTTAGE

4Bed/3Bath GREYSTONE COTTAGE
Ashland
9.4 out of 10, Exceptional, (11 reviews)
"Will definitely return. Beautiful house excellent location!"
United States
Christina J.
The price is NZ$794
includes taxes & fees
20 Apr - 21 Apr
4Bed/3Bath GREYSTONE COTTAGE

4-bedroom vacation home short drive to Huntington Mall, Marshall, & St. Mary’s

4-bedroom vacation home short drive to Huntington Mall, Marshall, & St. Mary’s
Ona
8.4 out of 10, Very good, (7 reviews)
"Well stocked kitchen and bathroom. We appreciated the communication with the owner. "
United States
Kim M.
The price is NZ$768
includes taxes & fees
1 May - 2 May
4-bedroom vacation home short drive to Huntington Mall, Marshall, & St. Mary’s

The Market Place by Nest and Bloom <br>Suite 4 (5045)

The Market Place by Nest and Bloom <br>Suite 4 (5045)
Ashland
9.6 out of 10, Exceptional, (4 reviews)
"Clean, well furnished, easy to find"
United States
Kelly S.
The price is NZ$491
includes taxes & fees
21 Apr - 22 Apr
The Market Place by Nest and Bloom <br>Suite 4 (5045)

Corner Cottage 2 bedroom pets welcome and close to downtown

Corner Cottage 2 bedroom pets welcome and close to downtown
Ashland
9.0 out of 10, Wonderful, (2 reviews)
"Very quiet, clean, nice house "
United States
Karen S.
The price is NZ$455
includes taxes & fees
23 Apr - 24 Apr
Corner Cottage 2 bedroom pets welcome and close to downtown

Secluded ranch home

Secluded ranch home
Ashland
10.0 out of 10, Exceptional, (16 reviews)
"Another great stay"
United States
Alix E.
The price is NZ$523
includes taxes & fees
12 May - 13 May
Secluded ranch home

The Blue House – Eclectic Art Haven Near Marshall & Huntington’s Best Parks

The Blue House – Eclectic Art Haven Near Marshall & Huntington’s Best Parks
Huntington
10.0 out of 10, Exceptional, (6 reviews)
"This is a wonderful place to stay!!!! The house is beautiful and elegant while also being cosy and comfy! All the small touches are a delight and made the experience restful and relaxing."
United States
Family M.
The price is NZ$543
includes taxes & fees
22 Apr - 23 Apr
The Blue House – Eclectic Art Haven Near Marshall & Huntington’s Best Parks

Cozy Fonzie Flat

Cozy Fonzie Flat
Ashland
10.0 out of 10, Exceptional, (1 review)
"It was a very pleasant stay, it was well maintained and clean. The property manager answered my questions quickly and efficiently,also was very professional. As a Veteran it was nice to have a place that accepts pets. "
United States
James F.
The price is NZ$483
includes taxes & fees
19 Apr - 20 Apr
Cozy Fonzie Flat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesapeake Hotel Reviews

Find out more about Chesapeake

Everything you need to know about Chesapeake holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesapeake holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesapeake. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake holiday rentals we have selected for you start as low as NZ$227 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesapeake rentals

At Expedia, we put the best Chesapeake holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesapeake rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Chesapeake?

Yes, there are holiday rentals close to the most popular sights in Chesapeake, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chesapeake has to offer?

2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.: This holiday home rental outside of Chesapeake is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

What can I see and do in Chesapeake?

Explore the area and family-friendly sights such as Camden Park Amusement Park, or get out into nature at a spot like Ohio River Valley. In the wider area, you’ll find Mountain Health Arena and Pullman Square.

What are holiday rentals like in Chesapeake?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesapeake. Holiday rentals offer amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family getaway.